How-to Tuesday: Turn Boring Small Talk into Deep Conversation

I can’t count how many times I’ve been stuck at a party or networking event without a friendly face nearby and it’s time to do the dreadful: approach a stranger and make small talk. Whether you hate this because a) you’re socially anxious or b) you simply dislike banal chit chat, I’ve figured out how to make the most of the situation. Here are a few of those stereotypical boring small talk topics and how you can manipulate them to your advantage and avoid awkward silence.

The Weather: Yes, we all know it’s so gross/humid/rainy/gorgeous outside. You’ve already probably said that six times today. Since you already know what the weather is like while you’re en route to the event, take that time to think about a related anecdote. For example: “Ugh it’s so rainy outside” turns into “Ugh it’s so rainy. I’m just glad this wasn’t the weather for the wedding I was at last weekend. The ceremony was outside and I don’t know what they would have done if it rained. It was actually a beautiful ceremony at a vineyard upstate. Have you been to that part of New York?” And now you’ve moved into a whole new conversation about weddings and wine and upstate New York and Fall foliage.

The Election: We are at election overload and talking politics can get dicey (take it from me, a Republican living in liberal NYC). Take this time to shift the conversation to something lighthearted. For example: “Did you watch the debate last night?” becomes “Did you watch the debate last night? It was nothing like the last time I saw Trump on TV for The Apprentice. Not a bad show, but I much prefer the Real Housewives franchise. My absolute favorite is New York. What about you?”

The Latest Celeb Gossip: If I have to hear one more thing about Brad and Angelina’s divorce, I’m going to vomit. Try immediately turning this into something you can talk about for a long time, like travel. You can always bring a conversation around to travel. “Did you know Brad and Angelina have a house in the French countryside? I’ve only ever been to Paris…have you ever been to the more rural areas? I’d love to learn more about it.”

Work: “Where do you work?” is always a go-to question. But if you don’t know anyone else who works at that company or you’re unfamiliar with the industry, you’re stuck. Also, after spending all day at the office, most people want to talk about something – anything – else. Switch the convo to the exact opposite of work: free time. For instance, I know nothing about finance so when someone tells me they work at Goldman, I always say something along the lines of “Oh wow, I know you must have some long hours. What do you do in your rare moments of free time? Like what did you do over the weekend?” The part about the weekend is important because unless you ask for specifics, most people will give you an “I dunno” when asked about themselves. Once they have the context of a time frame (this weekend, next weekend, this summer), they’ll likely open up. When they say they just want to hibernate with Netflix or a good book, you can then ask about the last good thing they’ve watched/read.